After a short-lived stint at the Berklee College of Music, where he had a "great learning experience, but not because of class," John Mayer set down roots in Atlanta, where his music career hit the ground running. After one year in Atlanta, he released his debut solo album, Inside Wants Out, in 1999. At the same time, he became a regular in the Atlanta club circuit, playing a steady stream of shows at venues like Eddie's Attic. An appearance in March 2000 at the South by Southwest Music Festival led to a recording contract with Aware Records, a subsidiary of Columbia. He began recording his major-label debut, Room for Squares, that fall with producer John Alagia, who had previously worked with artists like Dave Matthews and the Ben Folds Five.

Mayer's first album had been a decidedly acoustic effort; in contrast, Room for Squares featured a full electric band and showed the work of its producer with its funky hooks and an emphasis placed on Mayer's versatile, smooth voice, which bore more than just a stylistic resemblance to Dave Matthews. Columbia re-released Room for Squares in the summer of 2001, adding one bonus track, and also offered a very limited-edition two-CD set including a disc with two previously unreleased covers. Mayer's dedicated fan base grew substantially larger during his first cross-country tour to support the album, spawning a number of CD-R trading outlets through fan websites, as well as a successful live album, Any Given Thursday. Mayer's lucrative follow-up, 2004's Heavier Things, resulted in another Grammy, this time for Song of the Year. Looking to strip his sound down, he formed the John Mayer Trio with drummer Steve Jordan and bassist Pino Palladino. Their sold-out tour was documented on the 2005 release Try! John Mayer Trio Live in Concert